(5-methoxy-benzofuran-3-yl)-phenyl-methanone | 19303-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-methoxy-benzofuran-3-yl)-phenyl-methanone
• 英文别名: 3-Benzoyl-5-methoxy-benzofuran；(5-Methoxy-3-benzofuranyl)-phenylmethanone；(5-methoxy-1-benzofuran-3-yl)-phenylmethanone
• CAS: 19303-49-2
• 化学式: C₁₆H₁₂O₃
• mdl: MFCD00430824
• 分子量: 252.269
• InChiKey: WBIYZPQWXHJJEE-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  393.5±22.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-methoxy-benzofuran-3-yl)-phenyl-methanone 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以65%的产率得到4-methoxy-2-(5-phenyl-1H-pyrazol-4-yl)phenol
  参考文献：
  名称：

  Unexpected ring-opening of 3-aroylbenzo[b]furans at room temperature: a new route for the construction of phenol-substituted pyrazoles

  摘要：

  A new and convenient route for the synthesis of phenol-substituted pyrazoles 11-18 is starting from 3-aroylbenzo[b]furans 1-8 and hydrazine hydrate at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.085
• 作为产物：
  描述：

  (5-羟基-1-苯并呋喃-3-基)(苯基)甲酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (5-methoxy-benzofuran-3-yl)-phenyl-methanone
  参考文献：
  名称：

  Unexpected ring-opening of 3-aroylbenzo[b]furans at room temperature: a new route for the construction of phenol-substituted pyrazoles

  摘要：

  A new and convenient route for the synthesis of phenol-substituted pyrazoles 11-18 is starting from 3-aroylbenzo[b]furans 1-8 and hydrazine hydrate at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.085

文献信息

• Electronic Control on Linear versus Branched Alkylation of 2-/3-Aroylbenzofurans with Acrylates: Combined DFT and Synthetic Studies
  作者：Kolluru Srinivas、Yuvraj Dangat、Yadagiri Kommagalla、Kumar Vanka、Chepuri V. Ramana

  DOI：10.1002/chem.201700643

  日期：2017.6.1

  synergistic operation of the steric and electronic effects favoring the branched alkylation. Further DFT investigations on the alkylation of the isomeric 3‐aroylbenzofurans indicated a preference for the linear alkylation and this has been verified experimentally. Overall, the observed/calculated complementary selectivity in the alkylation of 2‐/3‐aroylbenzofurans with acrylates reveals that the substrate‐dependent

  通过计算与两个关键步骤相关的动力学（丙烯酸酯与中间钌环的配位），研究了控制2-芳基苯并呋喃与丙烯酸酯通过丙烯酸催化的羰基化CH活化的异常支化烷基化的因素。以及随后的迁移插入反应-借助DFT计算进行了研究。计算中考虑了每种烷基化方式的八个可能的方向。从这些计算中，已经理解，存在有利于支链烷基化的空间效应和电子效应的协同作用。DFT对异构3-芳基苯并呋喃的烷基化的进一步研究表明，偏爱线性烷基化，这一点已通过实验进行了验证。全面的，
• [EN] A PROCESS FOR THE PREPARATION OF ANTI-INFLAMMATORY AROYLBENZOFURAN COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS D'AROYLBENZOFURANNE ANTI-INFLAMMATOIRES
  申请人：COUNCIL OF SCIENT AND IND RSEARCH

  公开号：WO2015029062A1

  公开（公告）日：2015-03-05

  Disclosed herein an efficient process for synthesis of benzofuran analogues having anti-inflammatory activity which comprises, Ru-catalyzed branched and linear selective alkylation of aroylbenzofurans formula-I with alpha, beta unsaturated esters of formula-II via C-H activation in presence of base, additives and organic solvent at suitable temperature to give high yield of desired linear alkylated benzofuran compounds of formula-III or branched alkylated benzofuran compounds of formula-IV or mixture thereof.

  本文披露了一种高效合成具有抗炎活性的苯并呋喃类似物的过程，包括在碱、添加剂和有机溶剂的存在下，通过Ru催化的分支和线性选择性芳基苯并呋喃式-I与式-II的α，β不饱和酯进行烷基化反应，通过C-H活化在适当温度下，以高产率得到所需的线性烷基化苯并呋喃化合物式-III或分支烷基化苯并呋喃化合物式-IV或二者的混合物。
• Interrupting Base-Mediated Benzofuran Ring Transformation with Michael Acceptors
  作者：Kolluru Srinivas、Rashmi Sharma、Chepuri V. Ramana

  DOI：10.1021/acs.joc.7b01267

  日期：2017.9.15

  A simple two-stage approach for the synthesis of 3-(2-arylbenzofuran-3-yl)propanoates and propanamides has been developed employing simple acrylates and acrylamides and readily available 3-aroylbenzofurans. The key step of this process involves a base-mediated ring opening of the 3-aroylbenzofurans and subsequent Michael addition of the resulting 1,3-dicarbonyl intermediate with acrylate/acrylamide, followed by the deformylation in one-pot. The resulting products undergo an acid-mediated dehydrative cyclization to arrive at these targets.
• A PROCESS FOR THE PREPARATION OF ANTI-INFLAMMATORY AROYLBENZOFURAN COMPOUNDS
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US20160229827A1

  公开（公告）日：2016-08-11

  Disclosed herein an efficient process for synthesis of benzofuran analogues having anti-inflammatory activity which comprises, Ru-catalyzed branched and linear selective alkylation of aroylbenzofurans formula-I with alpha, beta unsaturated esters of formula-II via C—H activation in presence of base, additives and organic solvent at suitable temperature to give high yield of desired linear alkylated benzofuran compounds of formula-III or branched alkylated benzofuran compounds of formula-IV or mixture thereof.
• US9890132B2
  申请人：——

  公开号：US9890132B2

  公开（公告）日：2018-02-13